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On a rainy afternoon in Philadelphia, a young man walked into a Rolls-Royce dealership, curious because he’d never been close to such a pricey and prestigious car. He wore blue jeans and a matching jean jacket over an old sweater, with cowboy boots. His long brown hair settled on his shoulders, matching his moustache perfectly — a standard look for a 26-year-old professional hockey player from Niagara Falls in 1972. Especially for one nicknamed “The Turk.”

The Rolls-Royce dealer, wearing a three-piece suit, sniffed at his presence, folded up the newspaper he was reading and got up from his desk. He grudgingly acceded to The Turk’s request to unlock the front door of a burgundy sedan so he could size up the front seat.

“Sir, this is a long-wheelbase Silver Shadow limousine,” the dealer snorted. “Perhaps, if you purchased it, you’d be sitting in the back.”

The snooty treatment embarrassed Derek Sanderson, who had grown up poor. It made him mad, vindictive and then foolish. Sanderson went to the bank to get a cashier’s cheque for $78,000 (that’s more than $400,000 in today’s dollars when adjusted for inflation). He returned to the dealership, made sure the salesman didn’t earn a commission and drove the Rolls-Royce right off the lot.

A day earlier, the shaggy-haired Boston Bruins star of the late ’60s and early ’70s signed the richest contract in sports history — a $2.65-million deal with the Philadelphia Blazers of the WHA (surpassing Pelé on the highest-paid athlete list).

But signs of trouble developed immediately. For starters, the Rolls-Royce ran out of gas on the way home. Soon his bank account was running on fumes, too. Sanderson played only eight games for the Blazers in an injury-plagued first season. The team grew tired of the contrast between his lack of performance on the ice and his considerable energy off it.

He was a notorious partier, living in a constant haze of booze, drugs and women. After signing his contract with the Blazers, Sanderson covered a month-long excursion to Hawaii for seven people on his American Express gold card — a bill of close to $47,000.

“It was cheap then,” Sanderson says. “Draft beer used to be a nickel.”

The Blazers bought out his contract by the end of his first season. He returned to the Bruins in the NHL and was traded to the New York Rangers, where he continued to live lavishly. His substance abuse spiraled out of control. In 1977, Sanderson’s attorney informed him that he’d lost everything.

“How can I be broke?” Sanderson asked. “I can’t stay awake long enough to spend that much money.”

Years earlier, the hockey star had given power of attorney to the lawyer, a long-time family friend. The lawyer had made a string of bad investments, and that, along with Sanderson’s lifestyle, had drained his bank account. His reckless flamboyance left him with nothing more than nagging loneliness and a debilitating addiction to drugs and alcohol.

In the winter of 1979, Sanderson showed up in Chicago stoned. His long-time teammate and friend, Bobby Orr, checked him into rehab. In just a few years, he’d gone from being the world’s best-paid athlete to a drunk sleeping on a park bench.

It’s easy for sports fans today to find amusement in the financial train wrecks that many athletes suffer. But Sanderson says it’s important to consider the circumstances from which many athletes have come. It’s often forgotten that they started out from pretty average means, or worse.

Sanderson’s ridiculously opulent lifestyle was driven in part by watching his own father work for $26 a week sweeping floors, before becoming a machinist.

“It’s not a cultural thing. It’s not a white thing, a black thing, a Hispanic thing,” he says. “It’s a poverty thing.”

But Sanderson’s story didn’t end in financial tragedy. After hitting bottom in the late 1970s, he managed to pull himself up. He sobered up, got married and had two sons. He lectured about drug and alcohol awareness in schools and worked as a broadcaster in Boston. Along the way, he studied to become a financial advisor.

“I wanted to protect athletes from themselves,” he says. “I wanted to make sure they know what they own, why they own it and what they paid for it.”

He co-founded a sports wealth management group in 1990. In 2005 he went to work in the professional athletes department of Howland Capital, a private investment firm in Boston. While there, his clients often asked him, with a bit of concern in their voices, if he picked the stocks. (He didn’t.) Instead, he explained basic principles such as compound interest—how the $56,000 an athlete’s brother wants for a new SUV could be worth $600,000 when the athlete is 65, if properly invested.

He also shared his wild, almost unfathomable tales of life in the fast lane.

“It changes you,” he says of a young man’s fortune.

He told clients about the lessons he’s learned, about how lonely he felt surrounded by a world he purchased.

He told them about a shaggy-haired kid who was once the highest-paid athlete in the world. How he walked into a Rolls-Royce dealership and pulled out in a dream. And about how quickly the gas gauge said empty.

A modified version of this story originally appeared in the June 4, 2012, issue of Sportsnet magazine.

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